HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → Ethyl cis(+/-)-6-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-2-methylpyrimidine-4-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Ethyl 6-chloro-2-methylpyrimidine-4-carboxylate | HCID 71464314 | — |
| Reactant | cis(+/-)-4-Chloro-5-ethyl-N-(3-methoxypiperidin-4-yl)-1H-imidazole-2-carboxamide hydrochloride | HCID 86648695 | — |
| Product | Ethyl cis(+/-)-6-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-2-methylpyrimidine-4-carboxylate | HCID 86648718 | 21.4% |
Reaction Steps
The same operation as in Example (158a) was performed using cis(±)-4-chloro-5-ethyl-N-(3-methoxypiperidin-4-yl)-1H-imidazole-2-carboxamide hydrochloride obtained in Example (159a) (94.7 mg, 0.29 mmol), ethyl 6-chloro-2-methylpyrimidine-4-carboxylate (56 mg, 0.28 mmol) (reference: Bioorganic and Medicinal Chemistry Letters; 14; 15; 2004; 3869-3874) and diisopropylethylamine (108 mg, 0.84 mmol), to obtain 27 mg of the title compound as a yellow brown oily substance (22%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08536197B2 |
| Source dataset | uspto-grants-2013_09 |
| ORD ID | ord-99342a84f49b430db5f8092a19e7414a |
| Source note | uspto-grants-2013_09 |